Day 3 challenge

Goal: automate your daily stand-up preparation

Theme: foundation week - calendar intelligence

Time investment: ~10 minutes

Welcome to Day 3! Yesterday you experienced how Sidekick researches and creates calendar events. Today we’re going deeper into calendar intelligence—having Sidekick understand your schedule and automatically draft your daily stand-up updates.

This is where you see the power of agents that understand context, not just commands.

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What you’ll accomplish today

  • Ensure your Google Calendar connection is active
  • Have Sidekick analyze your day’s schedule
  • Generate a draft stand-up update based on your meetings
  • Experience how agents interpret calendar context

This isn’t about reading your calendar aloud. Sidekick analyzes meeting patterns, identifies priorities, and suggests talking points for your stand-up.

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Step 1: verify your calendar connection

If you completed Day 2, your Google Calendar should already be connected. Let’s verify and explore what Sidekick can see:

Ask Sidekick:

What meetings do I have today? Can you see my calendar?

Sidekick should be able to:

  • List your meetings for today
  • Show meeting times and attendees
  • Identify meeting types (1:1 s, team meetings, external calls)

If your calendar isn’t connected, follow the connection steps from Day 2. Sidekick guides you through the OAuth flow.

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Step 2: request your stand-up draft

Now for the magic. Instead of manually reviewing your calendar and thinking about what to share in stand-up, let Sidekick do the analysis:

Based on my calendar today, can you draft my morning stand-up update?
Include what I'm working on, any blockers you can identify from my schedule, and what I focus on today.

Watch how Sidekick:

  • Analyzes your meeting types and identifies work streams
  • Spots potential scheduling conflicts or back-to-back meetings
  • Suggests priorities based on meeting importance and attendees
  • Drafts talking points in a natural, conversational tone

Agent learning moment: notice how Sidekick infers context from calendar data, and how it’s interpreting patterns and making intelligent suggestions.

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Step 3: refine your stand-up style

Your stand-up format might be different from Sidekick’s initial draft. Let’s teach it your team’s style:

Our stand-ups follow this format:
- Yesterday's accomplishments
- Today's priorities (max 3 items)
- Any blockers or help needed

Can you redraft my update in this format? Also, our team prefers bullet points over paragraphs.

Sidekick adapts the content to match your team’s preferred structure and communication style.

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Step 4: identify intelligent insights

Ask Sidekick to go beyond basic calendar reading:

Looking at my schedule, what patterns do you notice?
Are there any potential issues or opportunities for improving my day?

Sidekick might identify:

  • Time blocks: “You have three 1:1 s back-to-back 2–3:30 PM”
  • Preparation needs: “Your client presentation at 4 PM follows immediately after your team planning session”
  • Travel time: “Note the location change between your 10 AM and 11 AM meetings”
  • Energy management: “Consider scheduling buffer time before your most important calls”

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What just happened?

In just 10 minutes, you’ve experienced sophisticated calendar intelligence:

Context understanding Sidekick doesn’t just read calendar entries—it interprets meeting types, identifies work streams, and understands priorities

Pattern recognition It spots scheduling conflicts, preparation opportunities, and ways to optimize your approach

Communication intelligence It adapts content format and tone to match your team’s communication style

Proactive insights Beyond the immediate request, it offers strategic suggestions for time management

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The power of calendar intelligence

Unlike static calendar apps, Sidekick understands the story your schedule tells. It can identify when you’re overbooked, suggest optimal meeting prep time, and even recognize when you need buffer time between high-stakes meetings.

Tomorrow - Day 4

Daily agenda preparation with contextual notes. Learn to have Sidekick prep your entire day with meeting insights and action item tracking.

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Pro tip for today

Before tomorrow’s session, try this experiment:

If you were managing my calendar, what changes would you suggest for tomorrow to make it more productive?

This teaches Sidekick to think strategically about your time management, not just report what’s scheduled.

Time to complete: ~10 minutes

Skills learned: calendar intelligence, automated content generation, context interpretation, communication style adaptation

Next day 4 - Daily agenda preparation with contextual insights

Remember every interaction teaches Sidekick more about your work patterns, communication style, and priorities. The agent is learning your preferences to become more helpful over time.